77373-46-7

Upstream product

• 4651-91-6 3-cyano-2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene 
• 100-47-0 benzonitrile 
• 108-94-1 cyclohexanone 
• 109-77-3 malononitrile 

Relevant academic research and scientific papers

Exploring the scope of the Gewald reaction: Expansion to a four-component process

An efficient four-component reaction was developed to take advantage of the reactivity of the 2-aminothiophene-3-carbonitrile functionality, which is obtained during the classical three-component Gewald reaction. Various α-methylene bearing ketones were reacted with malononitrile, elemental sulfur, and aryl/heteroarylnitrile derivatives in t-BuOH/NaOH to afford 2-arylthieno[2,3-d]pyrimidin-4-amines in high yields. Preliminary studies revealed the photophysical properties of the products and their potential for use as metal sensors.

Synthesis and Evaluation of Biological and Antitumor Activities of Tetrahydrobenzothieno[2,3-d]Pyrimidine Derivatives as Novel Inhibitors of FGFR1

A series of tetrahydrobenzothieno[2,3-d]pyrimidine derivatives were designed, synthesized, and evaluated as inhibitors of FGFR1. These analogs were synthesized via Gewald's reaction under mild conditions. The structures of the synthesized compounds were characterized by spectroscopic data (IR, 1H NMR and MS). Their antitumor activities were evaluated against H460, A549 and U251 cell lines in vitro. Results revealed that the tested compounds showed moderate antitumor activities. Structure-activity relationship analyses indicated that compounds with an aromatic ring substituted in the C-2 position or with larger molecules such as 3g, 4c, and 7 were more effective than others. The compound, 3g (78.8% FGFR1 inhibition at 10 μm), was identified to have the most potent antitumor activities, with IC50 values of 7.7, 18.9, and 13.3 μm against the H460, A549, and U251 cell lines, respectively. Together, the results suggested that tetrahydrobenzothieno[2,3-d]pyrimidine derivatives may serve as a potential agent for the treatment of FGFR1-mediated cancers.

Microwave-assisted synthesis of 4-amino-2-arylthieno[2,3- d ]pyrimidines and their subsequent functionalization

New 4-amino-2-arylthieno[2,3-d]pyrimidines were synthesized by reacting 2-amino-3-cyanothiophenes and aryl nitriles under microwave irradiation. Functionalization of 4-amino group was made by acetic anhydride and several isocyanates. Georg Thieme Verlag S

Reaction of Nitriles under Acidic Conditions. Part VI. Synthesis of Condensed 4-Chloro- and 4-Aminopyrimidines from ortho-Aminonitriles

Condensation of a nitrile with benzene, furan and thiophene ortho-aminonitriles in the presence of dry hydrogen chloride yields condensed 4-chloropyrimidines, condensed 4-aminopyrimidines or a mixture of the two condensed pyrimidines in varying proportions depending upon the nature of the nitrile and the substrate, ortho-aminonitrile.

Reaction of Nitriles under Acidic Conditions. Part I. A General Method of Synthesis of Condensed Pyrimidines

Nitriles are known to give rise to salts of different compositions with halogen acids.Many of the reactions undergone by nitriles under the influence of halogen acids are, in many cases, assumed to proceed via the intermediate formation of highly reactive